Timeless Style: How Any Woman Can Get This Look

Street Style Day 4 - Mercedes-Benz Fashion Week Istanbul - timeless style

Hoping to master timeless style and classic dressing? Here’s what you need to know | Timur Emek/Getty Images

We all love the chance to try something new in our wardrobes, whether it’s a unique new print or a trendy silhouette. But even if you’re an adventurous shopper who’s always open to trying on a new look, you have to admit that timeless style has its appeal. Sometimes, the most chic ensembles are the ones that look like they could have come out of any decade in the last half-century. Who hasn’t daydreamed about pieces that never go out of style, outfits that are simple and built of versatile essentials, and closets that are tightly edited? These are all benefits that go along with a focus on timeless style.

But as appealing as it sounds to be assured that your clothes are never going to look outdated when you look back on your Instagram selfies and Facebook profile shots years from now, achieving a classic look takes some thought. Which styles have actually stood the test of time? Which ones are going to continue to look chic and timeless in the future? What’s the best way to put together a wardrobe that’s precise and edited? And how can you avoid the perennial problem of having nothing to wear when your closet is filled to bursting?

And, more importantly, how can you make your classic wardrobe reflect your personal style? That’s a pursuit that often sounds diametrically opposed to the proclamations of lists claiming to have discovered the only “classic styles that every woman needs” or announcing the definitive canon of “investment pieces every woman should buy.” Those lists can help point you in the right direction. But the advice ahead will help you figure out how to plumb the depths of classic style for the styles that will become your personal favorites. It’ll also point you in the right direction as you figure out how to combine those pieces in ways that work for you.

Figure out your objective

Street Style: Day 5 - Milan Fashion Week SS16

If you’re interested in building a more classic wardrobe, start by figuring out what your goals are | Sebastian Reuter/Getty Images

Not every woman is interested in, or even thinks about, overhauling a wardrobe of modern, trendier pieces and opting for a timeless style of dressing instead. So figure out why a classic look appeals to you. Are you trying to avoid the same sort of cringe-worthy fashion mistakes and style missteps you made in high school or college? Does your interest in timeless style intersect with your desire for a simpler wardrobe? Are you finding little that you like at the mall, and realizing that you prefer sticking with the classics to experimenting with trends? Or have you determined that you want to buy clothing and accessories for keeps, and therefore need to invest in classic styles that won’t go out of vogue within a season or two?

All of these, and more, are valid reasons for shifting toward a more classic wardrobe. The upshot is that whenever you’re making a change to your style, the shift takes commitment — in terms of time, money, and perhaps even the self control it’ll take to pass up that cute but not-so-versatile sale find. If you can crystallize the reasons why you want to move toward timeless style, you’ll be able to figure out what you need to do to get to the wardrobe of your dreams.

Determine what kind of timeless style looks chic to you

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Next, figure out what kind of timeless style appeals to you, and which styles look classic and chic | Gabriel Bouys/AFP/Getty Images

Now comes the fun part: Finding the inspiration for the kind of timeless style that appeals to you. This may be exactly what the internet, the wide world of style blogs, and the depths of Instagram were made for. But another fun way to look for style inspiration is to check out some classic films (either from the local library or straight from your Netflix account). Take note of which decade or decades’ fashion is appealing to you. Do you find yourself drawn to the streamlined aesthetics of mid-century movie stars? How about the gamine clothing of the heroines of French New Wave films? Do you prefer the preppy look that appears through many decades of American movies?

There are many, many more examples, but the point is that your definition of “timeless style” might mean the glamorous dresses worn in the 1950s while your best friend’s could mean the casual, tomboyish styles that surfaced in the 1970s. Regardless of which specific style appeals to you, you can rest assured that there’s a way to make that style work for you today (and tomorrow, next year, and ten years from now). The goal is to have a clear picture — at least in your head, though an archive of photos on your phone or laptop of what you want to wear and what you want to look like wearing it would help, too.

Find your building blocks

Street Style Milan Fashion Week - timeless style

Finally, figure out which pieces are going to be your essentials and form the core of your wardrobe | Gabriel Bouys/AFP/Getty Images

Your next move is to simplify. Think back to the films, photos, and ensembles you liked, and figure out the essential pieces of clothing you’ll need to wear that look. If you’re going for timeless, remember that the goal is to look classic, not costume-y, so break down the looks you like into basic pieces that you won’t have trouble finding at your favorite stores. Your essentials might include a breton striped shirt or a white crewneck tee, a black leather jacket or a tan trench coat, a great pair of jeans or the perfect black pencil skirt. Whatever your look, break it down to its simplest elements to find the timeless style. If you plan carefully, you can identify a handful of classic pieces, colors, and silhouettes that you’ll be able to easily match with one another to create the look you want.

Depending on the current state of your wardrobe, this might entail a considerable amount of shopping and therefore, a good deal of time. But as you fill out your collection of essentials, you’ll gradually create a wardrobe stocked with clothes you love to wear and can see yourself wearing for a long time. Finally, this might be a good time to read up on our introduction to capsule wardrobes. Sure, this advice is aimed at simplifying the concept for men (who generally have fewer options in terms of styles and silhouettes than women), but the guide offers some useful advice on putting together a well-curated wardrobe from the building blocks of classic pieces — which is exactly what you’ll be doing as you make the shift toward timeless style.